By 1988 Michael could do almost no wrong on the charts. “Dirty Diana” was the fifth single off the Bad album, and when it hit the top of the Billboard Hot 100 that July, it did something no man had done before.
Five number one singles from one album. Katy Perry wouldn’t match that until 2011.
The song was a strange left turn for him. Loud and dark, nothing like the sweet pop people expected. Michael wrote it himself, and that howling guitar solo isn’t some session player you’ve never heard of. It’s Steve Stevens, the guy from Billy Idol’s band.
A year later the video picked up Number One Video in the World at the very first World Music Awards. Not the second one, the first. The whole ceremony was brand new that year, so being the one they handed that prize to meant something.
Here’s the setup before you watch.
Michael Jackson – Dirty Diana (Official Video)
Shot like a moody little concert film, all shadows and a screaming crowd. Watch for the moment that guitar takes over and Michael basically lets the song swallow him whole.
Now, about the name.
People always asked the obvious thing. Was Diana real? Michael swore she wasn’t. He said she stood in for every groupie who ever waited by a stage door, not one actual woman.
But there was one Diana he did worry about. A real one.
In July 1988 he played Wembley Stadium, and Princess Diana was out there in the crowd with Prince Charles. Michael got nervous. A song called “Dirty Diana,” belted out in front of a royal who happened to share the name? He decided to quietly pull it from the setlist to play it safe. “I took it out of the show in honor of Her Royal Highness,” he said years later.
Then she found out about it. And what she told him flipped his whole plan on its head.
I’m not going to spoil her reaction. Watch what actually happened that night instead.
Dirty Diana (Live At Wembley July 16, 1988) – MICHAEL JACKSON
This is fan footage of the real Wembley show, not an official release, but it’s the genuine performance from that summer night. Keep in mind who was sitting in the royal box while he sang every word of it.
Funny how it all worked out. The one Diana he tried so hard to protect turned out to be the one who wanted the song most.
And the record, the award, that screaming solo, none of it is the part people remember once they’ve heard this story.
Press play. You’ll get why.